In March, Legal Times reported on Craig’s first meeting with Obama at a 2003 fundraiser dinner held at the home of one of the Clintons’ closest friends, Vernon Jordan Jr. Jordan, now senior counsel at Akin Gump Strauss Hauer & Feld, told Legal Times that Craig had “been in love with [Obama] ever since” the dinner. And Craig said, "I became convinced that [Obama] had the ability to bring people together, and to end the partisan bickering in a way that no one else did."

Craig has known the Clintons since they all attended Yale Law School, but in March, he told Legal Times that he hadn’t spoken to them since the 2008 presidential campaign began. Craig served as a surrogate and foreign policy adviser during Obama’s campaign, and helped with debate preparation.